Tandem Radical Fragmentation/Cyclization of Guanidinylated Monosaccharides Grants Access to Medium-Sized Polyhydroxylated Heterocycles

The fragmentation of anomeric alkoxyl radicals (ARF) and the subsequent cyclization promoted by hypervalent iodine provide an excellent method for the synthesis of guanidino-sugars. The methodology described herein is one of the few existing general methodologies for the formation of medium-sized ex...

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Bibliographic Details
Published inOrganic letters Vol. 22; no. 21; pp. 8492 - 8495
Main Authors Santana, Andrés G, González, Concepción C
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 06.11.2020
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
free radicals
heterocyclic compounds
iodine
methodology
monosaccharides
Physical Sciences
Science & Technology
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Summary:The fragmentation of anomeric alkoxyl radicals (ARF) and the subsequent cyclization promoted by hypervalent iodine provide an excellent method for the synthesis of guanidino-sugars. The methodology described herein is one of the few existing general methodologies for the formation of medium-sized exo- and endoguanidine-containing heterocycles presenting a high degree of oxygenation in their structure.
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ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/acs.orglett.0c03091